I was cool once. Honestly. Some time in June 1995, for the duration of approximately 37 minutes, I was listening to Pavement and playing a vintage Telecaster and drinking bonded bourbon, and I was actually cool. It’s been all downhill since then, though, which is why I’m so grateful to the Library of America for “The Cool School: Writing From America’s Hip Underground,” edited by Glenn O’Brien. For starters, nearly every writer in this delightful collection can agree that whatever cool is, it’s not what it used to be, and it’s over, anyway.

Anatole Broyard wrote that “the hipster . . . had become a pretentious poet laureate. His old subversiveness, his ferocity, was now so manifestly rhetorical as to be obviously harmless” — in 1948! Jack Kerouac remembered that “when I first saw the hipsters creeping around Times Square in 1944 I didn’t like them either.” (Apparently, hating hipsters has a long and honorable history.) John Clellon Holmes waxed elegiac about “a vein of ironical decadence which, in those pious, prosperous years, ran deep in all of us” from the Olympian vantage of 1967. O’Brien notes that even the cult Brooklyn lit mag n+1 asked, “What Was the Hipster?,” emphasis on the past tense. It seems that cool comes into focus only in retrospect.

All anthologies are artificial arrangements, but an attempt to define a concept as inherently slippery as coolness is especially so. Fortunately, O’Brien’s version of the story — “a louche amuse bouche,” as he puts it in the foreword — is a good one. A downtown scenester who cut his teeth on the original version of Andy Warhol’s Interview, O’Brien is a magazine guy, and so his version of the underground express leans heavily toward nonfiction prose. As a curator of the offbeat, O’Brien gets an A-plus. Alongside the predictable names of Kerouac and Henry Miller and William S. Burroughs is a lot of weird, obscure stuff, bizarre fantasia from Brion Gysin and David Rattray and other marginal, semi-forgotten figures.

As a social historian, O’Brien is somewhat less successful. He locates the origin of cool in the inventive musicianship and heroin use of jazz icons such as Miles Davis and Lester Young, and traces it through the beatniks of the 1950s and hippies of the ’60s to the punks and avant-garde no wavers of New York’s East Village in the ’70s. The closer he gets to the present, though, the harder it is to see clearly, and the anthology sputters to an end with brief and unconvincing excerpts from Eric Bogosian and George Carlin.

A collection this diffuse thus reveals its pleasures piecemeal, including much that is familiar but worth revisiting. Amiri Baraka’s “The Screamers” is still vivid and sinuous, alive “with the secret perfume of poverty and ignorant desire,” and the excerpt from Joyce Johnson’s “Minor Characters” reaffirms that her memoir about life with Kerouac is demonstrably superior to anything Kerouac himself ever produced. To my mind, Hunter S. Thompson’s prose has lost none of its sizzle, Nick ­Tosches’s Vegas still swings hard, and the ineffable Lester Bangs’s verbal jousts with Lou Reed remain essential.

Better still are the unexpected revelations. The jazzy rhythms of Jack Smith’s meditation on trash-film icon Maria Montez mask a sophisticated manifesto on low culture that anticipates the hipster’s much-loathed embrace of irony and kitsch by a quarter-century. And “The Pop Imagination,” Holmes’s reminiscence of beatnik editor and impresario Jay Landesman, is a prescient masterpiece, a virtual catalogue of motifs that ring oddly familiar in the contemporary ear. A true original, Landesman “believed that artifacts were sometimes more evocative of their times than ideas” and he published his legendary magazine Neurotica for “the five thousand people who really make this society go — the opinion-makers, the guys with the crazy power, the Sell-Outs.”

It’s impossible not to hear in these words echoes of the current fetish made of the mid-century design object or the seemingly limitless obsession with tastemakers and trendsetters. And it’s no coincidence that O’Brien now writes for GQ magazine. In today’s hyper-inclusive electronic culture, it makes perfect sense that an arbiter of literary hipness should be employed by a magazine that makes a commandment out of commodification, and profits out of the endless cycle of enforced obsolescence. So in the end, the only permanent thing about cool is its transience.

Lindgren is a writer and musician who lives in Manhattan.


Writing from America’s Hip Underground

Edited by Glenn O’Brien

Library of America. 471 pp. $27.95